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Water → HCID 72312790, compound

HRID 2079220
Notes
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Reaction equation

HRID 2079220 reaction equation
[CH3:1][O:2][C:3](=[O:39])[N:4]=[C:5]([S:37][CH3:38])[C:6]([C:20]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[C:22]([O:28][Si](C(C)(C)C)(C)C)[C:21]=1[F:36])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(OCC)(=O)C.O>C1COCC1>[CH3:1][O:2][C:3](=[O:39])[N:4]=[C:5]([S:37][CH3:38])[C:6]([C:20]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[C:22]([OH:28])[C:21]=1[F:36])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 72312770HCID 72312770, compound

Product 1

HCID 72312790HCID 72312790, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 0.76 g of {2-[3-(t-butyldimethylsilanyloxy)-5-ethyl-2-fluorophenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 30 ml of THF there was added 1.6 ml of TBAF (1.0 M, THF solution) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 hours, and then 200 ml of ethyl acetate and 100 ml of water were added. The organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order and dried over anhydrous magnesium sulfate, the desiccating agent was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (0.41 g) as a white solid.

Workup

  1. washThe organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe desiccating agent was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-c98f6915cbc740b08cfc58c7ee4217bc
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928228B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes